A big contract is not always bad, and a small contract is not always good. The same can be said for long or short deals. Of course, most of the contracts on this list are both big and long, which naturally exposes the team to more risk, but failing to pony up can also leave a team vulnerable.
Many teams in baseball have simply decided not to sign players beyond a certain length or dollar figure, which may keep them off this list but has likely cost them the prime years of their home-grown stars (sorry, Royals fans).
There are plenty of bad deals to choose from, and this is just a selection of some of the worst. Feel free to comment with your own nominees.
The Yankees gave AJ Burnett a five-year deal worth $82 million coming off a season in which he posted a 4.07 ERA and 1.342 WHIP. Granted he won 18 games and struck out 231 batters as well.
Burnett spent three seasons in New York, leaving with a 34-35 record and 4.79 ERA. Even worse for Yankee fans, he posted an ERA over five and WHIP over 1.4 in the playoffs. Of course, as soon as Burnett left New York, he returned to form.
Burnett went 16-10 with a 3.51 ERA and 1.241 WHIP for the Pirates in 2012, with the Yankees paying $11.5 million of his $16.5 million salary.
The Red Sox gave Carl Crawford a seven-year contract worth $142 million after a 2010 season in which he batted .307 with 19 HR, 90 RBI, 47 SB, 110 runs scored and 13 triples.
Two years into the contract, Crawford has batted .260 with 14 HR, 23 SB, 88 runs scored and 161 games played combined. He has also been traded to the Los Angeles Dodgers for essentially nothing but relief from said contract.
Crawford may yet restore his career to its prior glory, but there is no doubt that the Red Sox' return on their investment is among the worst per-dollar production in the free-agent era.
The Mets agreed to pay Johan Santana $137.5 million over six years. That is nearly $23 million per season. Now, some may object to his place on this list because he is 46-34 with a 3.18 ERA and 1.201 WHIP since signing that deal, but aside from Santana, only three starters made over $20 million in 2012.
To be worth the money he is making, Santana needed to be among the top echelon of starters on a yearly basis. He missed all of 2011 and made only 21 starts in 2012, going 6-9 with a 4.85 ERA. In 2009, Santana was No. 15 in ERA among starters and No. 19 in WHIP. In 2010, Santana was No. 15 in ERA and No. 21 in WHIP.
The Mets paid a perennial Cy Young contender salary and got one great year, two good years, one complete lost season and a bad 2012.
Technically, Ryan Howard was not a free agent when he signed this monster extension with the Phillies, but this contract might have the worst result of any of the others listed when it's all said and done.
The extension runs from 2012-16 with a team option for 2017. Through one season of the deal, Howard has played 71 games, batted .219 and posted a .718 OPS. That's 210 points below his career OPS when 2012 started.
Of course, the writing may have already been on the wall for this deal before Howard tore his Achilles in the playoffs. His average on-base percentage and slugging percentage had each fallen three years in a row before 2012.
With Howard turning 33 in two weeks, the Phillies could be looking at a really expensive Matt Stairs if Howard cannot turn things around soon.
Beginning in 2007, the Giants agreed to pay Barry Zito $126 million over seven years. Five years into the deal, Zito was 43-61 with a WHIP of 1.407. He magically improved in 2012, winning 15 games with a 4.15 ERA despite posting a still-unimpressive 3.89 WHIP and 5.6 K/9.
Now, the Giants get a partial pass on this contract, and Brian Sabean gets to keep his job because the team has won two championships over the span of the contract, making every penny paid to each player worthwhile.
That being said, Zito will have to impress teams in the final year of his contract to earn a multi-year offer once he hits free agency after 2013.
The Phillies serve only as an example of a growing trend in baseball of overpaying closers.
Jonathan Papelbon, Rafael Soriano and Jose Valverde combined for 206.2 innings in 2012, which is less than 21 starting pitchers threw by themselves, and those three made $31 million for the season. That's more than any major league player at any position.
Consider that 2012 saves leader Jim Johnson made $2.6 million. Runner-up Fernando Rodney made $1.75 million. Add 24-year-old superstar closer Craig Kimbrel to the list, who made just $590,000, and it seems relievers can be found cheap.
Papelbon made $157,142.86 per inning pitched. Justin Verlander, defending Cy Young Award winner and contender to repeat that title, made $83,998.32 per frame. Digest those numbers and try to defend eight-figure salaries to 60-inning per season pitchers.
Jason Bay went into free agency after the 2009 season coming off back-to-back 30-plus HR, 100-plus RBI, 100-plus R seasons. He signed with the New York Mets for four years and $66 million.
In the three seasons since then, he has played in just 288 games, batted .234 and mustered 26 HR, 124 RBI, and 128 R. In 2010, the Mets were No. 24 in runs scored and No. 26 in OPS. In 2011, they were No. 12 and 13 in those categories and in 2012 they were 23 and 25.
With Carlos Beltran in St. Louis and Jose Reyes in Miami, Mets fans may have to wait for some of that Santana and Bay money to free up before they can contend again.
Josh Beckett signed a four-year contract with the Boston Red Sox worth $68 million. While he was excellent in 2011, the first year of the deal, Beckett fell apart to the tune of 7-14 with a 4.65 ERA in 28 starts in 2012. Then, like the aforementioned Crawford, he was sent to L.A. in the Red Sox midseason salary dump.
Beckett is owed $15.75 million each of the next two seasons. His K/9 was his lowest since 2006. Red Sox fans just need to remember not to compare his stats in 2013, where he'll spend his starts in Chavez Ravine, Petco Park and AT&T Park as opposed to Fenway, Yankee Stadium and Camden Yards.
Another team that got off the hook with terrible contracts, the Toronto Blue Jays signed Vernon Wells to a seven-year deal worth $126 million.
Wells started off well in 2008, batting .300, but he battled injuries and was only able to play 108 games that season. Since then, he has batted .249 with an OPS of .736. The Angels mistakenly took on Wells' contract in a 2011 trade before realizing their mistake in 2012 and benching him for the emergent MVP candidate Mike Trout.
Wells' future is in question as the Angels have no shortage of talented outfielders. He has batted .222 over his last two seasons (208 games), but he will take some solace in his $21 million paycheck each of the next two seasons.
"Alex Rodriguez had 34 home runs, 120 RBI, 141 R, 17 SB."
No one would be surprised if they heard someone say that a few years ago. After all, he topped each of those numbers in 2007 alone, but sadly, those are his combined numbers from the last two years combined.
This is sad because Rodriguez is only halfway through his 10-year, $275 million deal with the Yankees. It is wrong to say Rodriguez had not earned a record-breaking contract. He was coming off a five-year stretch in which he won three MVP awards, and the season before he signed the deal he batted .314 with 54 HR, 156 RBI, 24 SB, and 143 runs scored.
In the first year of the deal, he hit .302 with 35 HR, 103 RBI, 104 R and 18 SB. By the third year, he had lost 30 points on his batting average, 30 runs scored and five home runs. In the fifth year of the deal, 2012, he batted .272 with 18 HR, 57 RBI, 74 R and 13 steals.
Brian Cashman surely shudders to think what the last three years may look like if the future Hall of Famer does not regain his stroke soon.